U.S. Pat. No. 3,838,057 to Barnes et al., issued Sept. 24, 1974, discloses toilet bars containing ethoxylated quaternary ammonium compounds, including ethoxylated, quaternized polyethyleneimines (PEIs) taught to be useful in the detergent, textile, and polymer industries, as anti-static and softening agents. These ethoxylated quaternized PEIs have the formula: ##STR2## wherein R.sub.1 is a compatible quaternary nitrogen substituent; n is at least 2; x is from 3 to 40; and X.sup.- is a compatible anion. Preferred compounds are those where R.sub.1 is a C.sub.8 -C.sub.22 alkyl group or the group: EQU R'COO(EO).sub.y --CH.sub.2 CHOHCH.sub.2 --
where R' is a C.sub.8 -C.sub.22 alkyl group and y is from 3 to 40. See also U.S. Pat. No. 4,179,382 to Rudkin et al., issued Dec. 18, 1979; U.S. Pat. No. 4,152,272 to Young, issued May 1, 1979; and European Application No. 2,085 to Rudkin et al., published May 30, 1979, which disclose ethoxylated quaternized polyamines having C.sub.10 to C.sub.24 alkyl or alkenyl groups attached to one of the nitrogen atoms useful as fabric softeners.
U.S. Pat. No. 3,671,305 to Brown et al. issued June 20, 1972, discloses zwitterionic monomers which form polymers used to treat films, sheets, and filamentary materials so as to give them a durable, hydrophilic, anti-static, anti-soiling, soil releasing finish. These monomers have the formula: ##STR3## wherein n is 0 to 10; R.sup.0 is hydrogen or methyl; Z is oxygen or --NH--; A can be a C.sub.2 -CH.sub.3 alkylene group (e.g. ethylene) when n is 1-10; R' and R.sup.2 can be C.sub.1 -C.sub.4 alkyl; A' is C.sub.1 -C.sub.4 alkylene; and R can be SO.sub.2.
U.S. Pat. No. 3,671,502 to Samour et al. issued June 20, 1972, discloses co-polymers useful as binders in the production of non-wovens. These co-polymers consist essentially of from about 5 to about 90% of a monomer having the formula: ##STR4## wherein R.sub.1 is hydrogen or methyl; A is oxygen or --NH--; R.sub.2 is ethylene, propylene, 2-hydroxypropylene or 2-acetoxypropylene; R.sub.3 and R.sub.4 are alkyl; n.sub.1 is 1 to 4; and X.sup.-1 is SO.sub.3 -- or CO.sub.2 --; and from about 10 to about 95% by weight of a hydroxyacrylate such as a polyglycerol acrylate/methacrylate having the formula: ##STR5## wherein R' is hydrogen or methyl; R" is hydrogen, methyl or hydroxy; n.sub.2 is O when R" is hydrogen or methyl (e.g. an ethylene group); and n.sub.3 is 2 to 4.
U.S. Pat. No. 3,301,783 to Dickson, et al., issued Jan. 31, 1967, discloses oxyalkylated, acylated, alkylated, carbonylated and olefinated derivatives of polyalkyleneimines, in particular polyethyleneimines (PEIs). For the oxyalkylated derivatives, the alkylene oxide (e.g. ethylene oxide) is reacted with the polyalkyleneimine in a mole ratio of from 1:1 to 1000:1, and preferably in a ratio of from 1:1 to 200:1. Among the ethoxylated PEIs disclosed are Examples 1-O.sub.7 and 1-O.sub.8 formed by condensing 105 and 200 moles, respectively, of ethylene oxide with a 900 M.W. PEI. The degree of ethoxylation calculates out to about 4.5 and about 8 ethoxy groups per reactive site, respectively. See also Examples 27-O.sub.5 and 27-O.sub.6 which disclose ethoxylated polypropyleneimines (M.W. 500) which have about 4 and about 8 ethoxy units per reactive site, respectively. Amongst the numerous disclosed uses of these polyalkyleneimine derivatives is a teaching that they are useful as detergents, softening agents, and anti-static agents. Preferred uses disclosed by this patent are as chelating agents, lubricating oil additives, emulsifying agents, and cutting oils.
U.S. Pat. No. 2,792,371 to Dickson, issued May 14, 1957, teaches a process for breaking petroleum emulsions with oxyalkylated tetraethylene pentaamines (TEPA). Ethoxylated TEPAs specifically disclosed include those having about 5 (Example 3aa), about 7 (Example 4aa), about 8.5 (Example 5a) and about 15.5 (Example Bc) ethoxy units per reactive site. Similarly, U.S. Pat. No. 2,792,370 to Dickson issued May 14, 1957, teaches a process for breaking petroleum emulsions with oxyalkylated triethylene tetramines (TETAs) including those having about 5.5 (Example 3aa), about 7.5 (Example 4aa), about 9 (Example 5a) and about 16.5 (Example Bc) ethoxy units per reactive site. See also U.S. Pat. No. 2,792,372 to Dickson, issued May 14, 1957, (oxyalkylated higher PEAs used to break petroleum emulsions); U.S. Pat. No. 2,792,369 to Dickson, issued May 14, 1957 (oxyalkylated diethylene triamines used to break petroleum emulsions).
U.S. Pat. No. 4,171,278 to Andree et al., issued Oct. 16, 1979, discloses cold water detergent compositions containing a detergent surfactant (e.g. anionic) and a hydroxyalkyl amine in a weight ratio of 100:1 to 1:1. The amine can have the formula: ##STR6## wherein R.sub.1 is C.sub.1 -C.sub.16 alkyl; R.sub.2 is H or C.sub.1 -C.sub.16 alkyl; R.sub.1 +R.sub.2 have 6-20 carbon atoms; R.sub.4 is H or methyl; m, n, and o, are each 0 to 3 and A is bridging group such as ##STR7## wherein R.sub.3 is H or methyl; x is 2 to 6; y is 1 to 3; and p is 0 to 3; the sum of m to p being 1 to 5.5, and preferably 1 to 2. See also German Patent Document No. 2,165,900 to Henkel, published July 5, 1973, which discloses a washing agent for graying prevention formed by the reaction product of a PEI with an alkylglycidylether and ethylene oxide (2-hydroxyethyl moiety at each reactive site).
There are several patents which disclose detergent compositions, shampoo compositions and the like containing slightly ethoxylated PEIs (ethylene oxide:PEI weight ratio of 4:1 or less) to enhance the deposition and retention of particulate substances such as antimicrobials. See, for example, U.S. Pat. No. 3,489,686 to Parran, issued Jan. 13, 1970; U.S. Pat. No. 3,580,853 to Parran, issued May 25, 1971: British Patent Specification No. 1,111,708 to Procter & Gamble published May 1, 1968, U.S. Pat. No. 3,549,546 to Moore, issued Dec. 22, 1970; and U.S. Pat. No. 3,549,542 to Holderby, issued Dec. 22, 1970.